Squaramide organocatalysts can catalyze reactions via dual binding modes that activate both the substrate and a nucleophile of appropriate p<i>K</i>a. We have demonstrated that masked acyl cyanide (MAC) reagents are applicable nucleophiles under these conditions. MAC reagents serve as an oxidation state 3 equivalent and were added to beta-nitrostyrenes in high yields and enantioselectivities using a chiral squaramide catalyst. This presentation will describe an extension of this reaction to achieve diastereoselectivity by choosing a substituted, cyclic beta-nitrostyrene. We have developed and screened achiral squaramide catalysts for this reaction, which provide a similar organized transition state and effective conversions but are much simpler to access in only two steps. The products can be converted to beta-amino acids and other small chiral building blocks of use in drug discovery.

Squaramide organocatalyzed diastereoselective addition of a masked acyl cyanide to a beta-nitrostyrene

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.